Acetonitrile → HCID 86629831, compound

Participants

Reaction Steps

Methyl isocyanate (0.148 mL, 2.39 mmol) was added to a stirred solution of 1-{4-amino-2-[(aminooxy)methyl]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-ol (prepared as described in Example 100, 600 mg, 1.99 mmol) in DMF (5 mL). A solid formed immediately. The mixture was stirred for 2 hours at room temperature, then was heated to form a solution to which acetonitrile (10 mL) was added. Crystals formed that were isolated by filtration and purified by chromatography using a HORIZON HPFC (silica gel, gradient elution with 5-20% 2 M NH3 in methanol/chloroform). The appropriate fractions were combined and concentrated to a solid that was dried in a vacuum oven overnight to afford N-{[4-amino-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methoxy}-N-methylurea as white crystals, mp 206-207° C.

Provenance & Evidence